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Reactions of 3,3,3-trichloro(trifluoro)-1-nitropropenes with 2-morpholinoalk-1-enes

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Abstract

The reaction of 3,3,3-trichloro(trifluoro)-1-nitropropenes with 2-morpholinoalk-1-enes affords the nitroalkylated Z-enamines whose subsequent hydrolysis results in 2-trihalomethyl-1-nitroalkan-4-ones.

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References

  1. F. Brower, H. Burkett, J. Am. Chem. Soc., 1953, 75, 1082.

    Article  CAS  Google Scholar 

  2. H. Burkett, G. Nelson, W. Wright, J. Am. Chem. Soc., 1958, 80, 5812.

    Article  CAS  Google Scholar 

  3. S. Iwata, Y. Ishiguro, M. Utsugi, K. Mitsuhashi, K. Tanaka, Bull. Chem. Soc. Jpn, 1993, 66, 2432.

    Article  CAS  Google Scholar 

  4. V. Yu. Korotaev, I. B. Kutyashev, V. Ya. Sosnovskikh, Heteroatom Chem., 2005, 16, 492.

    Article  CAS  Google Scholar 

  5. V. Yu. Korotaev, V. Ya. Sosnovskikh, I. B. Kutyashev, A. Yu. Barkov, E. G. Matochkina, M. I. Kodess, Tetrahedron, 2008, 64, 5055.

    Article  CAS  Google Scholar 

  6. A. Barański, Pol. J. Chem., 1982, 56, 257.

    Google Scholar 

  7. K. Tanaka, T. Mori, K. Mitsuhashi, Bull. Chem. Soc. Jpn, 1993, 66, 263.

    Article  CAS  Google Scholar 

  8. K. Tanaka, T. Mori, K. Mitsuhashi, Chem. Lett., 1989, 1115.

  9. R. Jasiński, A. Barański, Pol. J. Chem., 2006, 80, 1493.

    Google Scholar 

  10. H. Burkett, W. Wright, J. Org. Chem., 1960, 25, 276.

    Article  CAS  Google Scholar 

  11. O. Klenz, R. Evers, R. Miethchen, M. Michalik, J. Fluorine Chem., 1997, 81, 205.

    Article  Google Scholar 

  12. V. Yu. Korotaev, V. Ya. Sosnovskikh, M. A. Barabanov, A. Yu. Barkov, M. I. Kodess, Mendeleev Commun., 2010, 20, 17.

    Article  CAS  Google Scholar 

  13. A. Ya. Aizikovich, V. Yu. Korotaev, M. I. Kodess, A. Yu. Barkov, Zh. Org. Khim., 1998, 34, 1149 [Russ. J. Org. Chem. (Engl. Transl.), 1998, 34, 1093].

    Google Scholar 

  14. M. Molteni, R. Consonni, T. Giovenzana, L. Malpezzi, M. Zanda, J. Fluorine Chem., 2006, 127, 901.

    Article  CAS  Google Scholar 

  15. M. E. Kuehne, L. Foley, J. Org. Chem., 1965, 30, 4280.

    Article  CAS  Google Scholar 

  16. A. T. Nielsen, T. G. Archibald, Tetrahedron, 1970, 26, 3475.

    Article  CAS  Google Scholar 

  17. D. Seebach, J. Goliński, Helv. Chim. Acta, 1981, 64, 1413.

    Article  CAS  Google Scholar 

  18. M. A. Brook, D. Seebach, Can. J. Chem., 1987, 65, 836.

    Article  CAS  Google Scholar 

  19. F. Felluga, P. Nitti, G. Pitacco, E. Valentin, Tetrahedron, 1989, 45, 2099.

    Article  CAS  Google Scholar 

  20. F. Felluga, P. Nitti, G. Pitacco, E. Valentin, Tetrahedron, 1989, 45, 5667.

    Article  CAS  Google Scholar 

  21. A. Ya. Aizikovich, V. Yu. Korotaev, L. E. Yaroslavtseva, Zh. Org. Khim., 1994, 30, 989 [Russ. J. Org. Chem. (Engl. Transl.), 1994, 30, 1045].

    CAS  Google Scholar 

  22. H. Shechter, D. E. Ley, E. B. Jr. Roberson, J. Am. Chem. Soc., 1956, 78, 4984.

    Article  Google Scholar 

  23. W. L. F. Armarego, J. Chem. Soc. C, 1969, 986.

  24. J. Paleek, O. Paleta, Synthesis, 2004, 521.

  25. G. M. Sheldrick, SHELX-97, Programs for Crystal Structure Determination and Refinement, University of Göttingen, Göttingen (Germany), 1997.

    Google Scholar 

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Correspondence to V. Ya. Sosnovskikh.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 137–140, January, 2011.

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Korotaev, V.Y., Barkov, A.Y., Slepukhin, P.A. et al. Reactions of 3,3,3-trichloro(trifluoro)-1-nitropropenes with 2-morpholinoalk-1-enes. Russ Chem Bull 60, 143–147 (2011). https://doi.org/10.1007/s11172-011-0020-3

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  • DOI: https://doi.org/10.1007/s11172-011-0020-3

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